US4130413A - Heterocyclic phenyl ethers and herbicides containing same - Google Patents

Heterocyclic phenyl ethers and herbicides containing same Download PDF

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US4130413A
US4130413A US05/831,480 US83148077A US4130413A US 4130413 A US4130413 A US 4130413A US 83148077 A US83148077 A US 83148077A US 4130413 A US4130413 A US 4130413A
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sub
alkyl
halogen
phenyl
alkoxy
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Reinhard Handte
Gerhard Horlein
Helmut Kocher
Peter Langeluddeke
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Hoechst AG
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Hoechst AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms

Definitions

  • This invention provides novel heterocyclically substituted 4-oxyphenoxy-alkane-carboxylic acid derivatives of the formula ##STR2## in which R is halogen, CF 3 , NO 2 , CN, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio,
  • A is O, S, NH, or N-(C 1 -C 4 )alkyl
  • R 1 is H or C 1 -C 4 alkyl
  • Z is a group of the formula ##STR3## n is zero or 1 or 2, R 2 is H, C 1 -C 12 alkyl (optionally substituted by 1 to 6 halogen atoms, preferably F, Cl, Br and/or by OH, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio, C 1 -C 6 alkoxy-C 2 -C 6 alkoxy, halo-C 1 -C 2 alkoxy, methoxyethoxy-ethoxy, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, phenyl, oxiranyl and/or phenoxy which latter may be substituted once or twice by halogen or C 1 -C 4 alkyl); C 5 -C 6 cycloalkyl (optionally substituted by halogen or methyl); C 3 -C 6 alkenyl, halo-C 3 -C 6 -alkenyl or C 5
  • R 3 is C 1 -C 6 alkyl, phenyl-(C 1 -C 2 )-alkyl, the phenyl radical optionally being substituted once or twice by C 1 -C 4 alkyl and/or halogen, C 3 -C 6 alkenyl, or phenyl (optionally substituted once or twice by C 1 -C 4 alkyl and/or halogen)
  • R 4 and R 5 which are identical or different, are H, C 1 -C 6 alkyl, hydroxy-(C 1 -C 6 )-alkyl, C 5 -C 6 cycloalkyl, or phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen or CF 3 ), with the proviso that R 4 and R 5 cannot be phenyl at the same time; or wherein R 4 and R 5 together form a methylene chain having 2,4 or 5 CH 2 -groups in which one CH 2 group may be replaced by O, NH, or N(CH 3 );
  • R 6 is H or CH 3 ,
  • R 7 is H, CH 3 , or C 2 H 5 ,
  • R 8 is H, CH 3 , C 3 H 5 or phenyl
  • R 9 is C 1 -C 6 alkyl (optionally substituted one to three times by halogen), cyclopropyl, C 3 -C 6 alkenyl, phenyl, C 1 -C 4 alkylphenyl C 1 -C 4 alkoxyphenyl, halophenyl, trifluoromethylphenyl or nitrophenyl and
  • R 10 is C 1 -C 4 alkyl or phenyl (optionally substituted once or twice by halogen, CF 3 , NO 2 , C 1 -C 4 alkyl).
  • the alkyl, alkenyl and alkinyl radicals in R 1 to R 5 , R 9 and R 10 may have straight or branched chains.
  • Preferred compounds of formula I are those in which
  • R is halogen, CF 3 , NO 2 , CH 3 , methoxy
  • A is O, S, N--CH 3 ;
  • R 1 is H, CH 3 and Z has the indicated meaning.
  • Halogen preferably stands for fluorine, chlorine or bromine.
  • the compounds of formula I can be prepared by known methods from starting materials known per se, for example
  • the reactions are preferably carried out in inert aprotic solvents such as aliphatic or aromatic hydrocarbons, for example, benzene, toluene, xylene; acid nitriles, for example acetonitrile or propionitrile; ketones, for example acetone, methylethyl ketone, or methylisobutyl ketone; acid amides, for example dimethylformamide, dimethylacetamide, N-methylpyrrolidone, or hexamethyl phosphoric acid triamide, or dimethylsulfoxide, at temperatures from 30° to 250° C.
  • aprotic solvents such as aliphatic or aromatic hydrocarbons, for example, benzene, toluene, xylene
  • acid nitriles for example acetonitrile or propionitrile
  • ketones for example acetone, methylethyl ketone, or methylisobutyl ketone
  • acid amides
  • inorganic or organic bases for example metal alcoholates, tertiary amines, alkali metals or alkaline earth metal carbonates and hydroxides such as NaOh and KOH.
  • the reduction of acids or esters to the alcohols is preferably effected with complex metal hydrides such as LiAlH 4 in ethereal, anhydrous solvents. Owing to the fact that the reaction generally proceeds exothermally, outside heating is usually unnecessary.
  • the subsequent esterification with acid anhydrides or acid halides is carried out in inert solvents (as in process a) at temperatures of from 0° C. to the boiling point of the solvent with the addition of an organic or inorganic base, for example Na 2 CO 3 , K 2 CO 3 , pyridine, or triethyl amine.
  • Esterification of the alcohols with carboxylic acids is brought about by adding an acid-binding agent such as P 2 O 5 or by azeotropic extractive distillation of the acidified components.
  • an acid-binding agent such as P 2 O 5 or by azeotropic extractive distillation of the acidified components.
  • Carbamic acid halides and isocyanates can be reacted within the alcohols in the presence of bases under conditions similar to those used for carboxylic acid halides, generally at slightly higher temperatures, preferably of from 40° C. to the boiling point of the solvent used.
  • esters can be used which are reacted with amines, ammonia, or hydrazines.
  • the solvents used are preferably the same as in process (a) and the temperature applied range from 40° C. to reflux temperature.
  • the acids of formula I can first be transformed into the acid halides which are then reacted with ammonia, amines or hydrazines. To bind the hydrogen halide set free an at least equimolar excess of the base used is required.
  • alcohols or mercaptans other esters or thioesters of formula I can be prepared.
  • the transesterification is performed by acid or base catalysis.
  • the alcohol component to be reacted with the ester is preferably added in excess and the lower boiling alcohol set free is continually distilled off at the same rate as it is formed in the transesterification process.
  • the dehydration of amides to obtain nitriles is preferably carried out in aromatic hydrocarbons at temperatures of from 50° C. to the boiling point.
  • the subsequent addition of H 2 S is expediently performed in an autoclave in the presence of catalytic amounts of a base, preferably ethanolamine, at temperatures of from 50° to 150° C.
  • heterocyclic starting materials of formula II are according to the definition of A, correspondingly substituted 2-halobenzoxazoles, 2-halobenzthiazoles, 2-halo-1-alkyl-benzimidazoles or 2-halobenzimidazoles, which are obtainable by known methods, for example by halogenation of the corresponding 2-mercapto compounds or 2-oxo-compounds. (Cf. C.A. 59, pages 396 et sq; Am. Chem. J. 21, page 111 (1988)).
  • the phenols of formulae III and IV can be prepared, for example, by unilateral etherification of hydroquinone (cf. J. Org. Chem. 39, page 214 (1974), Soc. 1965, pages 954-73).
  • R 1 is other than hydrogen
  • the compounds of formula I have an asymmetric center and are generally present in the form of a racemate.
  • the racemates can be separated by usual methods into diastereoisomers.
  • processes (a) and (b) there may also be used optically active starting compounds of formulae III and V.
  • the compounds of formula I according to the invention have a strong activity both in pre- and post-emergence application, against a wide range of annular and perennial weed grasses, and simultaneously they are excellently tolerated by dicotyledonous crop plants and some cereals. Consequently, the compounds can be used to selectively combat annual and perennial weed grasses in crops.
  • Weed grasses against which the compounds of the invention are effective are, for example, wild oat (Avena), blackgrass (Alopecurus spp), meadow grass (Poa spp), raygrass (Lolium spp), annual and perennial wild millets (Echinochloa spp,, Setaria spp., Digitaria spp., Panicum spp., Sorghum spp.), Bermuda grass (Cynodon spp.) and couch grass (Agropyron spp.).
  • the compounds can therefore be used for the manufacture of herbicidal compositions, which preferably contain 2-95% of the active compounds of the formula (I). They are customarily formulated as wettable powders, emulsifiable concentrates, dusting agents, granules, etc.
  • Wettable powders are formulations which are uniformly dispersible in water and which, in addition to the active compound, also contain diluents or inert materials, wetting agents, for example, polyoxyethylated alkylphenols, polyoxyethylated oleylamines or stearylamines, alkylsulfonates or alkylphenylsulfonates and dispersing agents, for example sodium ligninsulfonates, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate or the sodium salt of oleyl-methyl-taurine.
  • wetting agents for example, polyoxyethylated alkylphenols, polyoxyethylated oleylamines or stearylamines, alkylsulfonates or alkylphenylsulfonates and dispersing agents, for example sodium ligninsulfonates, sodium 2,2'-dinaphthylmethane
  • Emulsifiable concentrates are obtained by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics, and adding a non-ionic wetting agent, for example a polyoxethylated alkylphenol or a polyoxyethylated oleylamine or stearylamine.
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics.
  • a non-ionic wetting agent for example a polyoxethylated alkylphenol or a polyoxyethylated oleylamine or stearylamine.
  • Dusting agents are obtained by grinding the active compound with finely divided solids, for example, talc, natural clays, such as kaolin, bentonite pyrophillite or diatomaceous earth.
  • Granules can be manufactured either by spraying the active compound onto adsorbent, granular inert material or by applying active compound concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or even mineral oils, onto the surfaces of carriers, such as sand, kaolinites or granular inert material. Suitable formulations can also be manufactured by the customary methods of manufacture of fertilizer granules, if desired in admixture with fertilizers.
  • adhesives for example polyvinyl alcohol, sodium polyacrylate or even mineral oils
  • the concentrations of the active compounds in the commercial formulations can vary.
  • the active compound concentration varies, for example, between 10% and 95%, the remainder consisting of one or more of the abovementioned formulation additives.
  • the active compound concentration is about 10% to 80%.
  • Dust formulations usually contains 5-20% of active compound.
  • the active compound content in part depends on whether the active compound is in a liquid or solid form and what granulating auxiliaries, fillers and the like are used.
  • the commercial concentrates may be diluted prior to application in the usual manner, for example by means of water in the case of wettable powders and emulsifiable concentrates.
  • Dusts, granules and sprayable solutions are generally ready for use without further dilution.
  • the amount of active compound necessary for obtaining the desired result depends on external conditions such as temperature, humidity, type of soil, stage of plant development etc. It can vary within wide limits, for example between 0.05 and 10.0 kg/ha of active substance but is preferably between 0.1 and 5 kg/ha.
  • the active compounds according to the invention can be combined with other herbicides, insecticides and fungicides.
  • a wettable powder which is easily dispersible in water is obtained by mixing
  • a dusting powder is obtained by mixing
  • a granular formulation consists, for example, of about
  • inert granular materials such as attapulgite, pumice and quartz sand.
  • the compounds according to the invention and specified in Table I exhibited a good action against Lolium. Some of the compounds were also effective against Echinochloa, Cynodon and Agropyron.
  • Seeds of the weed grasses Lolium and Echinochloa were sown in pots and allowed to germinated in a greenhouse. 3 Weeks after sowing, the plants were sprayed with wettable powder formulations of the compounds according to the invention and the results were evaluated after 4 weeks.

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US05/831,480 1976-09-10 1977-09-08 Heterocyclic phenyl ethers and herbicides containing same Expired - Lifetime US4130413A (en)

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DE2640730A DE2640730C2 (de) 1976-09-10 1976-09-10 Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel
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CN108059630B (zh) * 2016-11-08 2020-04-14 沈阳中化农药化工研发有限公司 一种6-氯代苯并噁唑氧基苯氧丙酰胺类化合物及其应用
CN106632122A (zh) * 2016-11-29 2017-05-10 江苏富鼎化学有限公司 苯并噁唑苯氧羧酸酰胺类化合物及其制备方法
CN106632122B (zh) * 2016-11-29 2019-05-14 江苏富鼎化学有限公司 苯并噁唑苯氧羧酸酰胺类化合物及其制备方法

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ZA775349B (en) 1978-07-26
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MY8000179A (en) 1980-12-31
SE437827B (sv) 1985-03-18
FR2364210B1 (pt) 1981-11-13
JPS5340767A (en) 1978-04-13
BR7705999A (pt) 1978-06-27
YU41020B (en) 1986-10-31
IL52921A (en) 1982-02-28
NL191209C (nl) 1995-03-16
YU214677A (en) 1983-02-28
ZM6977A1 (en) 1978-06-21
TR19923A (tr) 1980-04-30
GB1548847A (en) 1979-07-18
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MX5575E (es) 1983-10-19
BE858618A (fr) 1978-03-13
KE3000A (en) 1979-11-23
SU1074387A3 (ru) 1984-02-15
AU2870377A (en) 1979-03-15
CA1095042A (en) 1981-02-03
DD132046A5 (de) 1978-08-23
AR222966A1 (es) 1981-07-15
MW2377A1 (en) 1978-07-12
PT67017A (en) 1977-10-01
OA05766A (fr) 1981-05-31
JPS6133179A (ja) 1986-02-17
NL7709744A (nl) 1978-03-14
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PT67017B (en) 1979-05-14
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FR2364210A1 (fr) 1978-04-07
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IT1115392B (it) 1986-02-03
DE2640730C2 (de) 1983-08-25
HRP940703B1 (en) 1997-02-28
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